Hydrochloric Acid → HCID 69337884, compound

HRID 844839Notes

Reaction equation

HRID 844839 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:29])[N:22]([CH3:28])[C:23](=[O:27])[N:24]([CH3:26])[CH:25]=2)=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[ClH:31]>O1CCOCC1>[ClH:31].[CH3:1][O:2][C:3](=[O:30])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:29])[N:22]([CH3:28])[C:23](=[O:27])[N:24]([CH3:26])[CH:25]=2)=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69337165HCID 69337165, compound

Product 1

HCID 69337884HCID 69337884, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester (1.94 mmol, 0.811 g) in dioxane (5 mL) was treated with 4.0 N (5 mL, 20 mmol) hydrochloric acid in dioxane at room temperature and the solution was stirred for 0.5 h. By this time, a light yellow precipitate slowly formed. The solids were collected by filtration and were washed with hexane to afford 412 mg (60% yield), mp 187-193° C. The mother liquour was concentrated under vacuum and the residue was triturated with dichloromethane. The combined solids, which contained some starting material, were combined and dissolved in methanol. The major portion of the methanol was evaporated and dichloromethane was added to form a precipitate. The solids were collected and dried to obtain 330 mg (48%) of 4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester hydrochloride salt (mp 187-193° C.). EI-HRMS m/e calcd for C16H19N3O4 (M+H) 318.1454, found 318.1447.

Workup

  1. customBy this time, a light yellow precipitate slowly formed
  2. filtrationThe solids were collected by filtration
  3. washwere washed with hexane
  4. customto afford 412 mg (60% yield), mp 187-193° C
  5. concentrationThe mother liquour was concentrated under vacuum
  6. customthe residue was triturated with dichloromethane
  7. dissolutiondissolved in methanol
  8. customThe major portion of the methanol was evaporated
  9. additiondichloromethane was added
  10. customto form a precipitate
  11. customThe solids were collected
  12. customdried

Sources & evidence

ORD record
ord-0a059eb068d942d2b4b1a1a203d5dc0e
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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